N-Ethylaniline → Laquinimod

HRID 240213Notes

Reaction equation

HRID 240213 reaction equation
CO[C:3]([C:5]1[C:6](=[O:18])[N:7]([CH3:17])[C:8]2[C:13]([C:14]=1[OH:15])=[C:12]([Cl:16])[CH:11]=[CH:10][CH:9]=2)=[O:4].[CH2:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:20].CCCCCCC>CO>[CH3:20][CH2:19][N:21]([C:3]([C:5]1[C:6](=[O:18])[N:7]([CH3:17])[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([Cl:16])[C:13]=2[C:14]=1[OH:15])=[O:4])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 8900Heptane2×HCID 54680901HCID 54680901, compound

Product 1

HCID 54677946LaquinimodYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Laquinimod acid was prepared according to the method described in U.S. Pat. No. 6,875,869: 5-Chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester (3.0 g), N-ethylaniline (2 eq 2-2.88 ml), and heptane (60 ml) were heated and the volatiles, mainly heptane and formed methanol, (32 ml) distilled off during 6 hours and 35 minutes. After cooling to room temperature the crystalline suspension was filtered and the crystals were washed with heptane and dried in vacuum to yield laquinimod acid (3.94 g, 98%) as white to off-white crystals.

Workup

  1. customLaquinimod acid was prepared
  2. distillationdistilled off during 6 hours and 35 minutes
  3. filtrationwas filtered
  4. washthe crystals were washed with heptane
  5. customdried in vacuum

Sources & evidence

ORD record
ord-af15affcb75c4db198a9610cb960de0e
Source dataset
uspto-grants-2014_02
Patent number
US08647646B2

Reaction notes

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